My Sister Found Me Dressed Up and Everything Changed

The week of my eighteenth birthday was the most intense of my life up to that point, and that was saying something, because I’d already lived through things few guys my age could ever tell.

Ever since I’d moved to the city to live with my sister Carmen, the afternoons at home were mine. She was in college until five and also worked two days a week as an assistant at a law office, so between noon and late afternoon I had three or four completely free hours. Hours that, for the past month, I’d been using in a very specific way.

I put on her clothes.

It had started almost by accident one Tuesday when I had nothing to do. I opened her drawer looking for who knows what and found a black lace thong at the top. I put it on without thinking, like a reflex, and spent twenty minutes in front of the bathroom mirror unable to look away from my own reflection. That same day I went to see Marcos.

Marcos was fifty-three, with graying hair and a way of looking at me that made everything else disappear. We’d been together for two months. He already knew I liked dressing as a woman, and he was the first person to ask me out loud: to put on girl’s clothes to be with him. The first time I did it, he looked me up and down with that slow, direct gaze of his and told me he wanted me to be his woman. I spent several seconds not knowing how to breathe.

That first afternoon in women’s clothes ended with me on my knees in the living room of his apartment, my skirt hiked up to my waist and my thong pulled to one side. Marcos pulled his cock out of his pants without any hurry, put it in front of my face, and told me that if I wanted to be his woman I had to learn how to suck it like one. It was huge, thick, with a red, shiny head. I grabbed it with both hands and started sucking as best I could, choking every time he squeezed the back of my neck to make me take more of it in. Saliva dripped off my chin and stained my top. He pulled it out of my mouth and rubbed it across my lips, my cheeks, my closed eyes. “Like this, slut, learn,” he told me in a rough voice that made my cock tremble too. “This is my woman’s mouth.” Then he threw me facedown on the rug, ripped off my thong, and spit on my ass before shoving two fingers in all at once. I screamed into the floor and opened up wider for him. When he went in with his cock, I felt like he was splitting me in two; he covered my mouth with his hand and fucked me slowly at first, then at a savage pace that made the sofa creak against the wall. He came inside me, grabbing my hair, and made me stay still with his cock still hard until he felt the semen dripping between my thighs.

For my birthday, Marcos had promised something special. He wouldn’t tell me what it was, only that we were going to spend the whole day together and then stay the night until the next day. My first full night with him. The idea kept me awake until two in the morning, my hand buried in my thong, touching myself while thinking about how he was going to fuck me slowly, how many times, in what positions, how much of his load he was going to leave in my ass and my mouth.

I organized everything so it would work. I asked my parents for permission, telling them I was going to meet up with friends from school to celebrate my birthday. No problem. Carmen also knew I wouldn’t be home Thursday, but she thought it was exactly that: a get-together with classmates, nothing more.

On Wednesday at noon, when Carmen left for college, I put on the outfit I liked best. The green lace thong, the black miniskirt, the fitted top, the fishnet stockings, and the high heels I kept at the back of the closet. I stood in front of the mirror for a long time. No makeup yet, because I hadn’t dared take that step, but I still felt good. Very good.

I went out to the back patio to do laundry. I loaded the washing machine, poured in the detergent, pressed the button. When I turned around to go back inside, Carmen was standing two meters from the door, staring at me with her eyes completely wide open.

My heart stopped.

I couldn’t speak. I started trembling, very slowly, as if the ground had become unstable beneath my feet. Carmen came closer without saying anything. She walked around me slowly, one full turn, looking me over from head to toe with an expression I didn’t know how to read. Then she lifted my miniskirt and saw the green thong, which was hers.

“I didn’t know I had a little sister,” she said.

I stayed frozen, unable to make a sound.

“Why the scared face?” she asked. “It’s fine.”

Carmen waited with her hands in her pockets, unhurried.

“I’d already noticed someone had been in my drawers,” she went on. “Things weren’t left the way I leave them. But I never imagined this.”

She took one more step toward me and looked me in the eyes.

“Say something. Seriously, it’s okay.”

“Really?” I managed to say.

“Really.” She smiled. “I always wanted a little sister.”

Something loosened in my chest. I started breathing again.

We went inside. Carmen grabbed the notes she’d forgotten — that was what had brought her back — and put them in her backpack. Then she pointed to the sofa.

“I’ve got a little free time. Let’s talk.”

We sat together. She hugged me tight without asking, and I hugged her back just as hard. She smelled like coconut shampoo and that lavender lotion she’d used since we were little.

“Don’t feel bad about this,” she said. “It’s completely normal. And honestly, I’m glad to know. We’re going to get along much better now.”

I told her. Not all the details, but the essentials: that I’d been wearing her clothes for weeks, that I felt good like that, that I’d started little by little and it was already part of my everyday routine. I told her about Marcos, that we’d been together for two months, that he was the one who’d helped me explore that side of myself. And I told her that for my birthday we were going to spend our first whole night together.

Carmen listened without interrupting. When I finished, she looked at me for a moment and asked:

“And how’s he doing downstairs?”

It took me a second to understand the question.

“Huge,” I said. “He opens me all the way every time. The first time he put it in me I thought I wouldn’t be able to take it. Now I’m used to it, but it still burns for a while afterward.”

“You lucky thing!” she exclaimed, covering her mouth so she wouldn’t burst out laughing. “And does he eat you out? Does he lick your ass before he puts it in?”

“Everything,” I told her, red to my ears. “He gets me on all fours and licks me there until I beg him to fuck me.”

“My God,” Carmen said, fanning her face. “Mature men are something else. Twenty-year-old guys don’t know what a tongue is.”

I was so amused seeing her like that that I laughed too. That was the moment everything really relaxed. The strangest conversation of my life and also the easiest one I’d had in a long time.

“Now it’s your turn,” I said.

Carmen tucked her legs under her on the sofa and told me. Three men total: the first when she was in her final year of high school, a boy her own age who wasn’t much — two minutes and he came, she said, and didn’t even realize she had a pussy. Then a forty-eight-year-old college professor, with whom she really learned what pleasure was, and she described it to me without holding back: how he put her on top of the desk in his office, spread her legs, and ate her pussy until he made her come three times in a row before fucking her. And now Roberto, her boss at the law office, fifty-five, divorced, who waited for her Tuesdays and Thursdays after work.

“I love mature guys,” she said without the slightest shame. “They know what they’re doing. They have patience. They’re not in a rush like guys our age. Roberto keeps me fucking for two hours before he comes. He sucks me, licks me, puts it in me slowly, takes it out, puts it back in. I end up soaking wet and he never even gets tired.”

“Marcos is fifty-three,” I replied.

We looked at each other. And we both laughed at the same time, without needing to explain the joke.

“We’re exactly the same,” Carmen said.

“I couldn’t have imagined it,” I answered.

That night we had dinner together, calm and easy, without the distance that usually existed between us. Then we went back to the sofa with a glass of wine each and kept talking. About the men we liked, how they made us feel, the things we wouldn’t tell anyone else. Carmen told me how Roberto fucked her on the law office desk with the door locked, how he covered her mouth with his tie so she wouldn’t scream, how he came inside her and then sent her back out to attend clients with semen dripping down her thighs under her skirt. I told her how Marcos made me walk around his apartment in heels, how he made me kneel on the rug and suck his cock while he watched the news, how I swallowed everything when he came in my mouth. It was the conversation I never could have predicted before that afternoon, and also the best one I’d had in a long time.

“We should all get together,” Carmen said at some point, with the same casualness as if she were suggesting pizza.

I looked up.

“The four of us?”

“Yeah. You and Marcos, me and Roberto. A dinner, or whatever happens. We’ll see. You know what’s going to happen anyway. Two mature cocks, two horny little sisters. No need to play dumb.”

The idea ran through me from head to toe. Two sisters, two older men, one night with no fixed schedule. The image settled in my head with a clarity I couldn’t ignore: Marcos fucking me on all fours over the table while Carmen sucked Roberto’s cock beside us, the four of us swapping, Roberto prying my ass open with those thick old-man fingers while Marcos ate my sister’s pussy. My cock got hard under my skirt and I had to cross my legs so Carmen wouldn’t notice. Though from the way she looked at me, she definitely did.

“Sounds good to me,” I said, with a calm that had nothing to do with what I was feeling inside.

Carmen smiled, pleased with herself.

***

Shortly before midnight, Carmen got up from the sofa and went to her room. She came back with two gift-wrapped boxes and set them on the table.

“Happy birthday, little sister,” she said, holding them out to me.

I hadn’t realized it was midnight.

The first box was from her: foundation, eyeshadow in several shades, black eyeliner, four lipsticks in different reds, nail polish, fake nails, and mascara. I opened it slowly, looking at each thing as if it were something I’d never seen up close before. I didn’t know what to say. I hugged her hard and didn’t let go for a long while.

“With red lipstick on, when you suck Marcos off, you’ll leave his cock marked,” she whispered in my ear. “He’s going to love those red rings around the base. Men go crazy for that.”

The second came with a card signed by Roberto. A woman’s perfume, a slender bottle with white flowers drawn on the label. I opened the cap and smelled it: something jasmine, something warmer underneath, like vanilla or damp wood.

“I told him about you,” Carmen explained. “He thought it was great. He says he’s really looking forward to meeting you. I told him you’re sluttier than me. He got hard right there at his desk.”

I was speechless for a moment.

“Thank you,” I said at last. “Both of you.”

We kissed each other on the cheek and each went to her room.

In bed, with the makeup on the nightstand and the perfume open, filling the room with that jasmine scent, it took me a long time to close my eyes. I took off my thong and touched myself slowly, imagining Roberto’s thick hand spreading my ass cheeks while Marcos filled my mouth with his cock. I shoved two fingers up my ass thinking about the night ahead, biting the pillow so Carmen wouldn’t hear me on the other side of the hallway, until I came all over the sheets with a long shudder that left me empty. But I was also thinking about Carmen, about Roberto, about that possibility she’d put on the table so naturally.

Four people. One night. Everything still to be seen.

Marcos was coming to pick me up at nine.

For the first time in a long while, I was certain that what was coming would surpass everything I had allowed myself to imagine.